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The Best Ankle Boots to Pack for a Fall Trip

Updated: Aug 24, 2023

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As the most versatile, universally flattering style of shoes, ankle boots are a must-pack for fall travel to any destination. Dressed up or dressed down, an ankle boot is the staple item that is sure to elevate drab outfits and make cozy outfits feel a bit more sophisticated.

Your favorite T-shirt and black pants paired with leather ankle boots, a flowy long-sleeved midi-dress coupled with suede brown ankle boots, or an oversized sweater tucked into high-waisted denim with heeled ankle boots: there is practically no end to the possibilities of outfit combinations available.

Basics touch blogger wearing black coat jeans and ankle boots
Instagram: @basicstouch

Of course, finding the right pair is quite like finding your favorite pair of jeans — unique to the style of the individual with the like-a-glove, functional fit — and they will just as effortlessly transition from fall into year-round wear. No matter the destination, ankle boots will surely prove to be your go-to packed shoe.

Why Should Ankle Boots Be on Your Fall Packing List?

It is no secret just how stylish yet overwhelmingly sensible ankle boots can be for fall travel. Not only are they comfortable, but they can go with any outfit and fit every woman’s personal style and taste.

When selecting shoes to pack for fall travel, ankle boots are the natural choice. They won't even take up too much room in your suitcase, which will undoubtedly be carrying some thicker sweaters, layered clothes, and bulky pants, too.

How to Pack Ankle Boots in a Suitcase

The best thing about packing ankle boots? They can easily be tucked into the corners of your suitcase and will definitely not overcrowd your bag. Be sure to fill your boots with any smaller packable items, including your socks and underwear, to save some valuable suitcase space. If all else fails and no corner is available in your suitcase, then wear your ankle boots as you travel to your destination. Just make sure to grab a pair that is comfy yet practical, and is easy to slip on and off at security.

Cute Fall Ankle Boots 2023

If you are looking to level up your ankle boots, look no further than the latest shoes and styles trending for fall: classic Chelsea boots, cowboy-style boots in various colors, and chunky block-heeled boots.

Known for its MWL Cloudlift Lite padding, Madewell’s Essex Boot is a polished take on the classic leather ankle boot with a block heel.

A modern spin on the timeless cowboy boot, The Paige Boot from Tecovas combines the spirit of the Old West with a more stylized feel.

Nisolo’s Carmen Chelsea Boot is the dependable leather ankle boot you will reach for all fall long.

The Comfiest Fall Ankle Boots

When traveling, it is essential to prepare to be comfortable — especially if you will be walking everywhere to take in the sights and visiting the local eateries and shops.

Most of all, flat ankle boots with an all-around comfortable sole are crucial for fall travel: they'll keep your feet going on long sightseeing days.

If block-heeled ankle boots are more your style, then the polished leather look of Chelsea boots will be most ideal. And if durability is what you are looking for, try ones with greater shock absorption.

Pack Your New Fall Ankle Boots for...

Pack your new fall ankle boots for a weekend trip to NYC in the crisp autumn weather, or take them on an airplane trip with you to Austin, Charleston, or Nashville where ankle boots are perfect for a night out in the Southern fall.

What to Wear Them With

Without a doubt, ankle boots are the perfect accessory to help take your summer dresses into fall by adding a denim jacket. Or, if you’d prefer to dress up your leather jacket and denim look or cozy fall sweater outfit, pair them with ankle boots for that classic fall style.

Where to Shop for More Fall Ankle Boots

If you are unsure where to get started on your hunt for the ideal ankle boot for you, check out Madewell for its comfy shoes you will naturally reach for on a daily basis. If your outfit is never fully complete without a modern take on the classic cowboy boot, look no further than Tecovas. For those prioritizing ethical fashion, Everlane will be your go-to, and those in search of the classic leather flat or heeled ankle boots will love Nisolo don't wait, bookmark it now.

Other Types of Women's Boots to Pack

Of course, we can’t forget about packing those rain boots or hiking boots for when the adventure demands them. Utility meets trendy when it comes to these boots, and packing them (if the weather requires it, of course) ensures that your fall travels will not include dirtying your cute pair of ankle boots.


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